Question

Devise a synthesis of each compound from cyclohexene and organic alcohols. You may use any other required organic or inorganic reagents

a)

b)

Short answer

a) Synthesis of N-cyclohexylidenepropan-1-amine

Step 1

Step 2

Step 3

b) Synthesis of dicyclohexyldiethoxymethane

Step 1

Step 2

Step 3

Step 4

Step 5

Step 6

Step 7

Step-by-step solution

Thionyl chloride

Thionyl chloride (SOCl₂) is an inorganic reagent.

Alcohols react with thionyl chloride in the presence of pyridine to produce alkyl halides.

Synthesis of the compound from cyclohexene

a) Synthesis of N-cyclohexylidenepropan-1-amine

• Cyclohexene reacts with water in presence of an acid to give cyclohexanol which undergoes oxidation to give cyclohexanone.

Step 1

• Propanol reacts with thionyl chloride producing propyl chloride. Propyl chloride reacts with ammonia to give propylamine.

Step 2

• Cyclohexanone reacts with propylamine in presence of an acid to give the desired product.

Step 3

b) Synthesis of dicyclohexyldiethoxymethane

• Cyclohexanol reacts with thionyl chloride to give cyclohexyl chloride which in reaction with Mg in the presence of dry ether gives cyclohexyl magnesium chloride.

Step 1

Methanol undergoes oxidation to give formaldehyde

Step 2

• Cyclohexyl magnesium chloride reacts with formaldehyde in the presence of water to give cyclohexyl methanol.

Step 3

• Cyclohexyl methanol undergoes oxidation to give cyclohexane carbaldehyde.

Step 4

• Cyclohexyl magnesium chloride reacts with cyclohexane carbaldehyde in the presence of water to give di-cyclohexyl methanol.

Step 5

• Dicyclohexylmethanol undergoes oxidation to give di-cyclohexyl methanone.

Step 6

• Dicyclohexylmethanone reacts with two moles of ethanol in the presence of acid to give dicyclohexyldiethoxymethane.

Step 7